Last Girlboss Standing

The unvarnished story of Glossier CEO Emily Weiss’s rise — and why she’s so resilient.

Presley Ann, J. Kempin, John Phillips, Paul Morigi/Getty Images, rblfmr/Shutterstock

At a startup like Glossier, a surprise department-wide meeting means one of two things: layoffs or treats. So when the tech department of the beauty phenomenon — well, what was then its tech department — was asked to gather for a visit from founder and CEO Emily Weiss on a late spring day in 2019, a buzz ran through the blush-pink second-floor office. The company had just launched a redesigned online cart and checkout, and some 30 members of the tech team hung around, wondering: Were they getting some limited-edition Glossier merch, or maybe some of the Otherland candles that burned in the conference rooms? Some hoped it would be a team meal from Shake Shack — the well-connected Weiss recently had lured Danny Meyer to speak with employees.

Near the reception desk at the front of the office, a beaming Weiss thanked the group for their hard work. Her smile got wider as she presented the magician, with words to the effect of “what you all do is magic,” according to an employee who was there. As the man began seeking volunteers for card tricks, several employees fled via the back exit. Others scrambled to look busy, classic tech introverts desperately hoping to avoid forced interaction.

It was a rare misreading of the room for Weiss, who by age 33 had created a billion-dollar beauty company largely because of her ability to intuit what people want. With a digital army and a handful of products, the former beauty editor initiated a swing of the beauty pendulum — from full-face foundation and double contouring to fresh-faced, no-makeup makeup — and created the kind of brand whose name people wear on a sweatshirt (Karlie Kloss and Timothée Chalamet did). As drugstore beauty brands chased the Glossier look, Weiss started to say that the future of beauty was tech. She raised $265 million, much of it from venture capitalists best known for funding apps, and hired developers, engineers, and an executive from Amazon.

But to the software engineers frozen in fear of being asked to pick a card, tech wasn’t magic, as Weiss put it. They had been struggling for years to marshal disparate ideas for Glossier’s tech future. (Was it an app? A platform? A shoppable social network?) To them, the magician was evidence of what former employees described as a disconnect between what had made Glossier successful and what Weiss thought Glossier needed to become. (Bustle spoke with more than a dozen former Glossier employees for this story; Glossier declined to make Weiss or any current employees available.)

Weiss was at a crossroads, too: no longer the founder of a hot startup, not yet the CEO of a profitable firm. Once upon a time, a beauty entrepreneur in her position would either sell to a conglomerate like Estée Lauder or become such a conglomerate, where the creative work of branding becomes a sideshow to building factories and managing distribution. But “that’s the business model of the past,” says Luis Capelo, formerly Glossier’s data science lead and the head of the company’s machine learning group. “And Emily knows that something like Glossier is a cultural phenomenon. So if you don’t create new ways of becoming huge, you just become a morbidity of the past.”

Weiss at The Atlantic Festival in 2018.Paul Morigi/Getty Images Entertainment/Getty Images

How was Glossier going to become huge? Weiss liked to say that Glossier would be the next Nike — a company with cultural relevance, beloved products, and industry-advancing technology. She also liked to compare the company to Apple, saying Glossier’s pink pouches were as visible a sign of community as AirPods. Investors, meanwhile, would be looking for Glossier to “scale” — or to make money faster than it increased costs — and one proven way to do that is digitally.

But when unexpected meetings — labeled “transition meetings” — showed up on Glossier tech calendars in January of this year, this time it was layoffs. After some five years and no buzzy digital product, Weiss decimated the tech department and laid off 80 employees, roughly a third of the company’s corporate employees. Glossier “made some mistakes,” she wrote to the staff. “We prioritized certain strategic projects that distracted us from the laser-focus we needed to have on our core business: scaling our beauty brand.”

Looked at one way, the tech debacle was another story of a startup pivoting and losing its way. Looked at another way, the layoffs were a sign of Glossier’s — and Weiss’ — maturity. The beauty company was giving up on its biggest dreams in order to double down on its attainable ones. Caution, after all, is how a CEO avoids becoming a cautionary tale who chases vaporware at the expense of their core business — and ends up the subject of a streaming mini-series. But Glossier’s reality check raised another question, one which still hangs over Weiss, now age 37, and her cohort of mediagenic millennial entrepreneurs: Can a startup grow up without losing its magic?

“Magic” also happens to be the word Glossier employees fall back on the most when trying to describe Weiss’ own abilities. “Her brain just works differently from other people’s,” says Youn Chang, Glossier’s former head of supply chain. “She has this magical element.”

Chang was a fan of Weiss before she was her employee. In 2015, Chang was a global supply chain manager at Apple and moonlighting as a beauty blogger. Glossier was sold out of everything and Chang wrote to ask if they needed supply chain advice. At the time, Weiss was eager to recruit people from Apple and Facebook, and she seemed confident Glossier had its own allure.

When Chang came into the office sporting pink hair, Weiss asked if she’d colored it specifically for the interview. “I love Glossier, but not that much to dye my hair for this interview,” Chang told her. As Weiss did with many candidates, she asked about Chang’s horoscope. (In the company’s early days, Weiss used to print out the daily horoscopes and post them in the elevator.) Chang, who is now the founder of clean oral care brand Ojook, says Weiss was particularly interested in the rising sign, which purportedly tells a lot about how a person interacts with the external world.

Weiss had every reason to be confident. Her supply chain issues were a result of her brilliance and, as even her detractors are quick to admit, hard work. Glossier’s minimalist debut collection of four skin-forward products in 2014 was such a hit that when Boy Brow launched in 2015, the $16 product had a 10,000-person waitlist. Customers had bought a year’s worth in five months and Glossier couldn’t make them fast enough. At a time when most beauty brands wanted to get into the try-everything, buy-everything paradise of Sephora, Weiss figured out how to get customers to buy products without sampling them.

“Her brain just works differently from other people’s. She has this magical element.”

Little wonder, then, that when asked by an interviewer onstage at the Female Founders’ Conference how she thought about converting new customers, Weiss — in a Dries Van Noten dress and Isabel Marant sandals — cocked her head and turned toward the audience. “My head of comms will kill me because I’m going to say something really weird right now,” she said, opening her eyes wide and pulling a self-deprecating face. “But I think about it a little bit like, how are religions scaled?”

According to those who know Weiss, her self-assurance — “the confidence of Jeff Bezos,” as one early employee put it admiringly — predates her success. At Wilton High School in Wilton, Connecticut, Weiss was voted “Most Likely To Be Famous” and was known for her social ease. “I was pretty connected in high school, involved in a lot of things, but I couldn’t tell you who her friends were,” says one classmate, meaning Weiss seemed to be friends with everyone. (As Weiss would later write in her letter introducing Glossier: “Snobby isn’t cool, happy is cool.”)

Interning at Ralph Lauren while still a high school student, Weiss turned up in “glamorous, stylish” clothes she had designed and sewn herself, recalled her boss, Whitney St. John-Fairchild. She made such an impression that St. John-Fairchild found herself cold-calling Amy Astley and saying, you gotta hire this girl. “It was like a natural instinct for me to say to myself: ‘This girl is so genius I’m just going to call the editor of Teen Vogue,” St. John-Fairchild says. The 20-year-old Weiss, by this time an NYU art student building installations in Steinhardt School basements, took St. John-Fairchild to lunch on Madison Avenue — St. John-Fairchild thinks it was the celebrity favorite Nello — as a thank you. After three years at Teen Vogue, where Weiss was immortalized as “super intern” opposite Lauren Conrad on The Hills, she moved on to working as a fashion assistant at W and then Vogue. On a shoot with Doutzen Kroes in Miami, the model talked up an amazing self-tanner that didn’t smell, and Weiss thought: “My civic duty is to share this with the world.” A few months later, while still at Vogue, she started Into The Gloss, which took a voyeuristic approach to cool women’s beauty routines and medicine cabinets.

Before she started Into The Gloss, Weiss was Teen Vogue’s second most famous intern.

Even before Weiss pressed “publish” on the first ITG post, she knew it was going to be more than another beauty blog — and cold-called Lancôme to convince them to advertise (she says they sent a $5,000 check). Soon, ITG had a signature Warhol-esque photography style and an engaged community of product obsessives. (According to a Harvard Business School case study of Glossier, advertising revenue for the site reached $5 million.) Weiss, meanwhile, had a reputation as a down-to-earth boss determined to foster a beautiful workplace, even if it meant doing the dirty work herself. In the blog office on Howard Street, nobody knew it was Weiss who took the bathroom’s white hand towel home to wash every night until people jokingly complained about it looking dirty. Weiss looked sheepish. She had gotten so busy she’d missed a few days, she admitted. “It was endearing,” says an early employee. “It made you want to go to war for her.”

Four years after its launch, Into The Gloss raised $2 million in venture capital and became Glossier; four years after that, the company moved into a Soho office designed by architect Rafael de Cárdenas, a former Calvin Klein designer whose clients include Nike. Here, Weiss’ workplace vision was fully realized. Fashion and art world-beloved florist BRRCH supplied frequently-changing floral installations. Coconut waters, little cheeses, and fancy yogurts were meticulously arranged in the double-door, clear glass refrigerators. “If someone came and took a water, within 20 minutes all the waters would be pushed to the front so it always looked full and perfect,” says a former employee. The conference rooms were named after Frida Kahlo, Michelle Obama, and Ina Garten (the latter two were known Glossier fans). The smell of burning sage after-hours was no cause for concern. For the tech team, then set up at a WeWork, Weiss sent over a Byredo burning rose candle, even though it was forbidden at the coworking space, saying, “Guys, do it discreetly.”

At some startups, luxury design and amenities might be evidence of reckless spending. At Glossier, the company was simply living up to its brand values of beauty and community. And it worked: A workplace culture emerged in which young women knew they could ask the entire company for dry shampoo recommendations on the Ask Glossier Slack channel without fear of judgment. “I’ve been trying to recreate Ask Glossier at every company I’ve been at since without success,” says one former employee. The corporate culture was, for lack of a better word, empowering: so many employees went on to start their own businesses that they’ve been dubbed the Glossier mafia. “My positive experience at Glossier helped me create my brand,” says Chang. “Listening to its customers, creating unique and memorable experience and valuing community and interesting content — those are what made Glossier a phenomenon, not just another beauty company.”

The powder room at Glossier’s New York City office. (Photo via @Glossier Instagram)

Weiss may be a former Vogue staffer, but she is the anti-Anna Wintour. To decide Glossier’s first advertising campaign in 2014, Weiss pinned up dozens of images from the shoot in the conference room and let staffers vote on their favorites, using little colored stickers. “I remember feeling like she was taking a lot of things she probably experienced at Vogue and democratizing them and making it more fun,” says an employee from that time. Weiss will pause a Zoom meeting to introduce herself to an unfamiliar face and, in pre-pandemic days, she would often swing through the kitchen wearing cool boots to comment on how delicious some new yogurt looked. She wasn’t fazed when she stumbled on two employees bleaching their eyebrows for Halloween in the gender-agnostic bathrooms, with their cushy toilet paper and Aesop post-poo drops in every stall. “Don’t get bleach on the floor,” she said. She can be dishy (“Fun tip,” she told a podcaster in 2017, “I use our Milky Jelly cleanser as a vagina wash. It’s pH balanced.”) and is shockingly approachable for someone who has admitted on a podcast that she flew to Copenhagen for highlights.

Weiss prided herself on listening, like the time she edited a personal Instagram post at the behest of LGBTQ+ staffers. They objected to her posting a picture of her then-boyfriend and now fiance, Stripe chief product officer Will Gaybrick, with a single crystal on his nail and a caption wishing a Happy Pride to her sparkle princess. “She really wanted to have a sit-down with somebody to really understand what was going on,” recalled Taylor Staugas, a former UX designer who rose from the rank of intern.

“My head of comms will kill me because I’m going to say something really weird right now,” Weiss said. “But I think about it a little bit like, how are religions scaled?”

Capelo — a Harvard-trained programmer lured by Weiss’ plans for a groundbreaking technology offering — says Weiss never treated ignorance as an obstacle, an attitude he found useful when he left to start his own company. “She would say, ‘Oh, you don’t know how to do warehouse distribution? Let’s just find a warehouse.’ It was like everything was doable and everything was learnable and nothing seemed too hard to do, honestly,” he says. “She made it look, not easy, but she made it look really kind of achievable.”

Plus, Weiss was in it for the long haul. “L’Oreal has a male CEO, Estée Lauder has a male CEO, but the majority of beauty brands that those companies own are founded by women so generally the woman is the CEO for a while, and maybe once the company gets bought or sold or enough time goes by, the female CEO ends up going away,” she once told a podcast. “I don’t have any plans to go away anytime soon.”

At each stage of Glossier’s growth, Weiss proved her genius for devising beautiful, surprising moments. Glossier’s pink and white products, with their slight apothecary feel, were a bubble-wrapped delight to unbox, and its pop-ups and stores — which Weiss saw as physical unboxings — were a cross between art installations and pep rallies. When Melanie Masarin, Glossier’s then-head of retail, struggled to find a suitable pop-up space in San Francisco in 2018, Masarin suggested something out of the box: A beloved local fried chicken restaurant. Masarin, now the founder and CEO of non-alcoholic spirit company Ghia, says Weiss was immediately on board. “Emily said, ‘I don’t really understand this but I trust you, so go for it.’” Fantastical, expensive details abounded, like an undulating botanical sculpture for a Seattle pop-up in 2019, built by model-turned-artist Lily Kwong, which required a team of gardeners and grow lights to keep hundreds of outdoor plants alive indoors in low light.

At times, opening stores seemed to take precedence over selling stuff. “We would joke about how much money they spend on pop-up stores when they don’t even know if we’ll be sold out of [products], or whatever the operational problem was at that point,” Chang says. “Or we’d be told we needed to save money because we needed to meet the timeline for the pop-up store, which would be so enormously expensive.” Disney CEO Bob Iger visited for one of Weiss' fireside chats — she was a whiz at tapping her network for employee enrichment — and Weiss frequently compared Glossier to Disneyland. She likened the retail employees (showroom editors, in Glossier parlance) to characters like Mickey Mouse that guests make a pilgrimage to go meet and take pictures with. The customers weren’t the only ones making pilgrimages. Greer Clarke, a former recruiting coordinator, once discovered that a candidate had somehow worked at every pop-up, including London. “I don’t know how they managed that, just moving around-wise,” she says. “Hats off to them.”

Maintaining Glossier’s cool required saying “no” to anything off-brand, and on this front Weiss was decisive. Showing a product on a complete range of skin tones would, in theory, make more customers feel comfortable adding to cart. But if some photos didn’t pass muster with Weiss, says a source who saw it happen, those skin tones might not end up represented on the site.

Glossier Seattle. (Photo via @Glossier Instagram)

She was exacting about the products, too. When customers complained about the Generation G lipstick breaking, Weiss made reformulating and repackaging it a top priority. “Even though not that many people had a problem with it and it was expensive,” Chang recalls, “she did it.” When the company realized the mascara it had proudly launched as vegan turned out not to be so — it contained beeswax — Weiss proactively refunded every customer who had bought it before the copy was updated. And when Weiss discovered, uncharacteristically late, that her customers cared about sustainability, the company’s Glitter Gelée eye shimmer was scrapped (its glitter was plastic, which is to say, non-biodegradable), as was what one former employee remembers as $100,000 worth of unsustainable packaging. “If you do that multiple times a year, it really adds up in terms of waste,” says the source.

Creatively, Weiss is a generational talent. But she’s part of a generation of entrepreneurs expected to deliver runaway, industry-disrupting growth, which puts the normal tension between creative and business on steroids. That tension came to a head during the 2019 launch of Play, a colorful makeup sub-brand that was perhaps ahead of its time. She brought in an external creative director (a friend and DJ/music producer), according to a source, then brought it back in house. The launch was scheduled for March and, in December, management was still debating whether Play needed its own website. And if Play did need its own site, how long would that take to build? Production and photography cost $1.5 million, says a source. According to another former employee, when Play got to Weiss for review, she cut all the model shots of two products, including Vinylic Lip, a click-pen lacquer, because she didn’t think the gloss looked glossy enough.

Weiss shut down Play less than a year later. But talking to former employees, it’s not an exaggeration to say it remains a source of collective trauma. When some of the tech team would play the card game Werewolf, where someone gets murdered at night and the next morning everyone discusses who did it, the moderator would change the setting from a medieval village in the woods to “the night before the launch of Glossier Play, we’re all just trapped here, and so-and-so is dead in the kitchen, with Cheerios all over the place.”

Play was a flop, but Glossier had never been stronger. Two weeks after the colorful sub-brand launched in 2019, the company was valued at $1.2 billion after closing a $100 million funding round led by Sequoia Capital, an early investor in PayPal, Zoom, and Reddit. In retrospect, these were the last days of direct-to-consumer companies with grand tech ambitions, of perplexingly well-funded companies selling discount razors and eyeglasses, of “we’re not a mattress company, we’re a sleep data company.” Weiss told Bloomberg that Glossier had entered “phase two,” in which it would cut out Instagram and Facebook by building the perfect social media platform for beauty. Customers would connect over dewy looks, discover products automatically detected in beauty tutorial videos, and make purchases, all within the Glossier app, which the company began developing in 2018. It required users to give their star sign when they signed up.

Building such an ecosystem proved to be a personnel challenge. In designing events and retail spaces, Weiss put her faith in people with good taste and, when it came to beauty products, she hardly needed anyone. “The process really is all driven by Emily,” says Capelo. “She values her own intuition more than any expert advice.” In her Steve Jobs-y way, she identified beauty problems distressing her digital community and developed products that solved them. Weiss worked hard to recruit former Facebook and Instagram executive Keith Peiris as head of digital product, calling on her network of business luminaries to talk up the job to him and sweetening the deal, says a source, with a referral for an interior designer for his apartment. Sources say that Peiris lasted barely six months. He was replaced by Maykel Loomans, from Facebook, who also barely lasted a year.

“People couldn’t stand up to Emily and didn’t know how to tell her, ‘We need to make a decision and you can’t make a change after this.’”

In the beauty world, Glossier was Valhalla, but, in tech, there’s always another high-paying job at Google or Instagram. Engineers say they didn’t feel set up for success at a company whose strength was image-making. On the tech team’s floor in the Soho office, meeting rooms were erected from Glossier’s signature pink glass with decals. The walls looked amazing, but they couldn’t be written on. (The tech team was eventually given some rolling whiteboards that a former employee says teams would fight over using.) A prolonged period of company-wide restructuring and leveling delayed promotions, which tech companies offer like clockwork, and accelerated a talent exodus.

Weiss’ eye for detail and her perfectionism — so essential to her beauty products — was fundamentally at odds with the way tech products are built, which is to get it out fast and fix it later. Some of the people Weiss trusted were anxious that putting out a buggy app in beta might tarnish Glossier’s luster. On the tech front, says Staugas, Weiss wanted to listen and learn. “She was super open to feedback and wanted it even if she didn’t necessarily know who to go to for the right feedback, especially internally,” says Staugas. Weiss could be decisive, but she could be just as quick to reverse her decision.

And just because she sought advice didn’t mean it was given to her candidly. “People couldn’t stand up to Emily and didn’t know how to tell her, ‘We need to make a decision and you can’t make a change after this,’” says a former employee. Employees openly wondered: Was love of one brand enough to sustain a whole social network? “The research was pretty cut and dry that if there was a community experience on the website it would be so biased toward Glossier it wouldn’t be interesting to people,” says another former employee, and yet the debates persisted. One concept for the app involved sharing the contents of your medicine cabinet; the app would recognize the products and allow you to buy them. But would it only recognize Glossier products or would Glossier start selling other brands? The vision was so unclear the app began to be referred to internally by some as “the quote unquote app,” the employee says.

Glossier employees honored Timothée Chalamet, who wore a Glossier hoodie to an event for the film Uncut Gems.

According to Steve Blank, an adjunct professor teaching entrepreneurship at Stanford University (and serial startup founder who once appeared on the cover of Wired two months before he realized his startup was going bankrupt), it’s not uncommon for a startup to fundraise off the back of tech that is still undefined. “They probably realized that saying ‘tech’ was increasing their valuation,” he says. “All startups kind of do that. It’s buzzword bingo, and it worked.” Nor is it uncommon for a founder to wake up one day and realize that the problems facing their company no longer interest them. As Blank points out, the people who are constant innovators are not the same people who typically want to run a thousand-person company. His own exit point, he said, was usually around 800 people, when he realized he was “solving HR issues, not creativity issues.”

Around this time, no amount of palo santo could cleanse the atmosphere. Members of the tech team began slowing their pace if they saw Weiss getting into an elevator. “There was a lot of doom and gloom and general jaded-ness and people over their jobs,” says Staugas. “And Emily was very optimistic about things, almost ignorantly so. Like we’d be worried about a project and she just had a completely different tone or attitude or wasn’t really recognizing the problems we were recognizing.” With each new leadership hire, tech employees wondered if these people would persuade Weiss to get rid of the app.

In late 2019, Weiss added two female Amazon executives to the C-suite, chief operating officer Melissa Eamer and chief technology officer Pawan Uppuluri. At the same time, leadership started paying closer attention to spending — under the guidance of a new CFO, Vanessa Wittman, according to a source close to the company. The pricey fresh raspberries and blueberries in the kitchen were dialed back and Doritos arrived (“We were like, ‘Are you going to say something?’” says one former employee), and the company cut back on shipping inventory via air. Weiss’ taste remained exact. She wanted luxury necklaces for a holiday campaign that would have made it impossible for Glossier to make its 80% profit margins (standard for beauty companies, and one reason for the celebrity makeup line gold) and felt out of reach for the average Glossier shopper. “Our consumer base wasn’t luxury. It’s supposed to be inclusive,” says a former employee. The person added: “She also obviously has a different lifestyle than I think most of her consumers, which is kind of hard.”

Glossier’s behind-the-scenes struggles made what played out publicly in 2020 even more remarkable. In short: Weiss closed all three stores, laid off the entire retail staff, faced allegations of mishandled racist incidents that undermined her company’s progressive branding, and — unlike female executives under similar fire at The Wing, Away, Everlane, and Refinery 29 — survived atop her company. Current and former Glossier employees watched as story after story was written about so-called girl bosses and dissected them via text messages and Slack channels but “in the end I don’t think the parallel is really there,” says a longtime employee who left in 2020. Even though this employee was unhappy with decisions Weiss was making when they left (and blames these decisions on investors), they say, “I am still in awe of her. I still respect her.” Another former employee — an Away alum who left the suitcase company because of undermarket pay and a “super toxic” work environment — says she had “a great time at Glossier” and attributes Weiss’ longevity to how good she is with people, and how much she loves Glossier (something nearly everyone interviewed noted).

“I am still in awe of her. I still respect her.”

Still, a small anti-Glossier backlash had been brewing before the pandemic, with TikTok beauty influencers posting takedowns of the company’s limited shade ranges, and it blew up in August of 2020. Earlier that summer was the height of the George Floyd protests, and Glossier made a $1 million donation split between racial justice causes and Black-owned beauty brands. To many of the roughly 150 Glossier showroom editors who were were furloughed in June and laid off in August, the gesture reeked of hypocrisy. About 50 of them, calling themselves “Outta The Gloss,” wrote an open letter accusing the brand of failing to protect them from racist customers and micro-aggressing managers, fostering a culture that hampered BIPOC employees’ success.

The criticism came at a vulnerable moment. Pre-pandemic, pop-ups provided a burst of new customers in new markets, and, without these, growth stalled. Quarantine was all about self-care, but after an initial sales surge put many Glossier products out of stock, the company overcorrected and ordered too much, says a former employee who worked in that department. Throw a cultural crisis on top of a turbulent economic moment, and it’s not hard to imagine a young founder’s firm grip on her company shaken loose in favor of what Blank calls “adult supervision.” He says that in industries that depend on the creativity of the founders, smart investors often “bring in somebody” — he cites Sheryl Sandberg at Facebook as an example — “who actually cares about spreadsheets and finance and can read an income statement and cash flow and balance sheets.”

But if Weiss was rattled, she didn’t show it. She didn’t over-apologize, and instead announced steps Glossier would take and how the company would account for them. The tech team hastily revived a decommissioned blog feature so that her message could appear on the company’s own website.

Nobody interviewed for this story was surprised that Weiss withstood the blowback. One former longtime employee says the racism experienced at the retail level simply did not go all the way to the top. “I’m sure things happened at Glossier that don’t deserve to be minimized, but I don’t think it could be traced to Glossier’s overall culture or the way Emily acted,” they said. They remembered an incident from the company’s early days, when a co-worker talked about how she’d gone as Jennifer Lopez for Halloween, complete with a big fake butt. A note went around to all of the roughly 30 employees saying this kind of thing wasn’t OK, that it didn’t fit with Glossier’s values. In 2021, the launch of Cleanser Concentrate, Glossier’s follow-up to its hit Milky Jelly Cleanser, was delayed when the company realized debuting it during the trial and verdict of Derek Chauvin might send the wrong message.

Internally, few saw the tech department layoffs coming. Glossier was still filling tech positions in November 2021, says a source with direct knowledge. But to those watching the space, Glossier’s un-pivoting made sense. Venture investment in cash-burning direct-to-consumer companies has slowed down, according to PitchBook, especially after some high-profile disasters. (See Casper, once valued at $1.1 billion, recently sold for about $300 million, or less than the $350 million it raised.) Many venture capitalists have moved on, some to software-as-service type companies. Others, including Forerunner Ventures’ Kirsten Green, an investor who gave Weiss a chance and also backed Warby Parker and Dollar Shave Club, are focused on “more B2B type business.” (Green did not respond to interview requests.)

Direct-to-consumer is “a dangerous space to be in,” says Elizabeth Edwards, who invested in Peloton and Freshly before going on to found her own firm, H Partners. When most direct-to-consumer startups, including Glossier, were scaling, the cost of acquiring customers on Instagram, Google, and Facebook was cheap. But ad costs on those three platforms have increased 300 percent a year on average in the last decade, according to Edwards’ analysis, and shipping prices have surged. Still, she says, “if you have the right touch,” you can make it without partners like Ulta and Sephora — and it also happens to be a good time to be negotiating retail leases. “If you crush it in experience, if people are saying, ‘this is lovely, this is a vacation, this is something I’m not getting at Sephora’ … If people see a reason to keep going into the store, that loyalty is so great because so many people forget that brick-and-mortar is also a place to discover,” Edwards says.

A return to in-real-life shopping experiences plays to Weiss’ strengths as a CEO. She’s an effective saleswoman of, well, everything. (Says Staugas, who is not a fangirl: “Every time Emily talks, it is inspiring.”) Her cultural antennae remain perfectly tuned, and she has been — as always — listening. In January, Glossier relaunched its popular You Solid perfume, but with a vegan formulation and an eco-friendly refillable sculptural pink swivel compact. Within a week, it was nearly sold out.

Glossier’s Los Angeles store, opened in November 2021.

Weiss spent most of the pandemic in Los Angeles with Gaybrick, with whom she is now expecting a baby, due in June. (She has pointed out on Instagram that Glossier’s new After Baume for Face “is also an amazing belly butter.”) In November 2021, her new hometown saw Glossier’s triumphant return to in-person retail with a giddy, whimsical, and dog-friendly pink palace that takes up nearly a block of Melrose. Featuring 17-foot versions Boy Brow and Cloud Paint and a pandemic-friendly outdoor space, it’s a nod to Glossier’s past and present, with a surrealist marble fountain and pink coffees and matchas from LA’s chic Alfred. On opening day, fans lined up to snag the LA-exclusive merch: a keychain shaped like a ‘90s-era flip phone, with a mirror inside you can use to check your Glossier Ultralip. And Weiss was there, charming shoppers (“I visited with my daughter and her friend last Saturday (they loved meeting you),” one posted on her Instagram), watching editors pack orders, and tearing up that people were back.

Back at corporate, Glossier was making another commitment to the physical world. In October 2021, Glossier applied to trademark the playful, wave-topped tables where lip balms and face serums are displayed in stores. Table design might seem like an unusual next move, unless you consider which other titan of branding — a company whose retail dominance inspires many CEOs — once battled to trademark their distinctive store design: Apple.